55282-87-6Relevant academic research and scientific papers
Selective Aerobic Oxidation of Primary Alcohols to Aldehydes
Shibuya, Masatoshi,Furukawa, Keisuke,Yamamoto, Yoshihiko
, p. 1554 - 1557 (2017/08/11)
The 2-azaadamantane- N -oxyl (AZADO)- and 9-azanoradamantane- N -oxyl (nor-AZADO)-catalyzed selective oxidation of primary alcohols to the corresponding aldehydes is described. The use of tert -butyl nitrite as the co-catalyst enables efficient aerobic oxidation in MeCN instead of previously reported AcOH; this is important for the selectivity of the reaction. The addition of a solution of saturated aqueous NaHCO 3 after the completion of the reaction was effective to suppress the overoxidation of the product to the corresponding carboxylic acid during the workup.
An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes
Trost, Barry M.,Livingston, Robert C.
experimental part, p. 11970 - 11978 (2009/02/05)
Catalytic ruthenium complexes in conjunction with an indium cocatalyst and Broensted acid isomerize primary and secondary propargylic alcohols in good yields to provide trans enals and enones exclusively. Readily available indenylbis(triphenylphosphine)ruthenium chloride, in the presence of indium triflate and camphorsulfonic acid, gives the best turnover numbers and reactivity with the broadest range of substrates. Deuterium labeling experiments suggest that the process occurs through propargylic hydride migration followed by protic cleavage of the resultant vinylruthenium intermediate. Application of this method to the synthesis of leukotriene B4 demonstrates its utility and extraordinary selectivity.
Vinylcyclopropylacyl and polyeneacyl radicals. Intramolecular ketene alkyl radical additions in ring synthesis
De Boeck, Benoit,Herbert, Nicola M. A.,Harrington-Frost, Nicole M.,Pattenden, Gerald
, p. 328 - 339 (2007/10/03)
Treatment of a variety of substituted vinylcyclopropyl selenyl esters, e.g. 11, with Bu3SnH-AIBN in refluxing benzene leads to the corresponding acyl radical intermediates, which undergo rearrangement and intramolecular cyclisations via their ketene alkyl radical equivalents producing cyclohexenones in 50-60% yield. By contrast, treatment of conjugated triene selenyl esters, e.g. 32, with Bu3SnH-AIBN produces substituted 2-cyclopentenones via intramolecular cyclisations of their ketene alkyl radical intermediates. Under the same radical-initiating conditions the selenyl esters derived from o-vinylbenzoic acid and o-vinylcinnamic acid undergo intramolecular cyclisations producing 1-indanone and 5,6-dihydrobenzocyclohepten-7-one respectively in 60-70% yields. A tandem radical cyclisation from the α,β,γ, δ-diene selenyl ester 31 provides an expeditious synthesis of the diquinane 35 in 69% yield.
Synthesis of γ-Hydroperoxy-α,β-unsaturated Carbonyl Compounds from α,β,γ,δ-Unsaturated Carbonyl Compounds by Cobalt(II) Porphyrin-catalysed Hydroperoxygenation
Matsushita, Yoh-ichi,Sugamoto, Kazuhiro,Nakama, Tuyoshi,Matsui, Takanao
, p. 567 - 568 (2007/10/02)
γ-Hydroperoxy-α,β-unsaturated carbonyl compounds are prepared in good yields by the regioselective hydroperoxygenation of α,β,γ,δ-unsaturated carbonyl compounds with molecular oxygen and triethylsilane in the presence of cobalt(II) porphyrin as a catalyst.
Sulfones as chemical chameleons. Heteroatom substituted allyl sulfones as conjugative reagents
Trost, B. M.,Ghadiri, M. Reza
, p. 433 - 442 (2007/10/02)
3-Phenylthio-1-phenylsulfonylprop-2-ene, Z-3-methoxy-, and Z-3-benzyloxy-1-phenylsulfonylprop-2-ene serve as valuable building blocks wherein the sulfone imparts both nucleophilic and electrophilic properties to the allyl moiety.Alkylations of the corresp
REACTIVITY OF THE 1-t.BUTYLTHIO-3-METHOXY-1-ALKENES TOWARDS METALATING AGENTS, II. ALLYLIC DEPROTONATION OF THE E-ISOMERS AND OF THE Z-PROPENYL DERIVATIVE.
Ruel, O.,Ekogha, C. Bibang Bi,Julia, S. A.
, p. 4829 - 4832 (2007/10/02)
Deprotonation of the title compounds with a lithiating agent and subsequent alkylation furnish the 1-substituted products 4.The 1-t.butylthio-3-methoxy-1-lithio-1-alkenes 3 become new equivalents of the hypothetical anions I.
